N6,N6,N6-Trimethyl-L-lysine (CHEM021850)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:58 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021850
Identification
Common NameN6,N6,N6-Trimethyl-L-lysine
ClassSmall Molecule
DescriptionN6,N6,N6-Trimethyl-L-lysine, also known as epsilon-N-trimethyl-L-lysine or n6,n6,n6-trimethyl-l-lysine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. N6,N6,N6-Trimethyl-L-lysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N6,N6,N6-Trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. N6,N6,N6-Trimethyl-L-lysine participates in a number of enzymatic reactions, within cattle. In particular, N6,N6,N6-Trimethyl-L-lysine and S-adenosylhomocysteine can be biosynthesized from L-lysine and S-adenosylmethionine; which is catalyzed by the enzyme histone-lysine N-methyltransferase SETD7. In addition, N6,N6,N6-Trimethyl-L-lysine and oxoglutaric acid can be converted into 3-hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid; which is mediated by the enzyme n6,n6,n6-trimethyl-l-lysine dioxygenase, mitochondrial. In cattle, N6,N6,N6-trimethyl-L-lysine is involved in the metabolic pathway called carnitine synthesis pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2-Amino-6-(trimethylammonio)hexanoateHMDB
(S)-2-Amino-6-(trimethylammonio)hexanoic acidHMDB
delta-TrimethyllysineHMDB
epsilon-N-Trimethyl-L-lysineHMDB
epsilon-Trimethyl-L-lysineHMDB
N(6),N(6),N(6)-Trimethyl-L-lysineHMDB
S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminiumHMDB
TrimethyllysineHMDB
6-N-L-Trimethyl-L-lysineHMDB
epsilon-N-Trimethyl-lysineHMDB
TRIMETHYLLLYSINEHMDB
Trimethyllysine hydroxide, inner salt, (S)-isomerHMDB
Trimethyllysine, (+-)-isomerHMDB
Trimethyllysine hydroxide,inner salt, (+-)-isomerHMDB
Trimethyllysine chloride, (S)-isomerHMDB
(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acidHMDB
Chemical FormulaC9H20N2O2
Average Molecular Mass188.267 g/mol
Monoisotopic Mass188.152 g/mol
CAS Registry Number19253-88-4
IUPAC Name(2S)-2-amino-6-(trimethylazaniumyl)hexanoate
Traditional Namen-trimethyllysine
SMILESC[N+](C)(C)CCCC[C@H](N)C([O-])=O
InChI IdentifierInChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1
InChI KeyMXNRLFUSFKVQSK-QMMMGPOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP-3.2ALOGPS
logP-6.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.63 m³·mol⁻¹ChemAxon
Polarizability21.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-9300000000-17fb5edf4cea1b4dcafdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-6900000000-f1602619e61c625d69c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-932e6c169445b94455b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-5900000000-1a10f83950431edf55b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-da852a06c44090497022Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-259b17dcbcd89ac303fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001i-5900000000-34a50370b70a804c255bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-0a0007f7f545c6797887Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-3900000000-853327bd0e39b33319f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0019-2900000000-7bc743d45af1a8804ef1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9000000000-226e1500e9ae9494b4bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-5182d0d6a3ab64a06c09Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-d5736c9d1d529490c9b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-628513f87fa53b8eb808Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-dff395556a2686da0f1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-5900000000-b01e2dbf67baf33ef6e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-9eb55f6f4d8669a538a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0536-9000000000-7dc3464380609c193782Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-0f467f0c771ad5024ac5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0900000000-6306038d328c591e1128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01y7-2900000000-44354c8813190fe25a0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-9400000000-499e4dafbd41d754a57dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3bc9f6f2c730e7f3785cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-9928cba63f73f9126887Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-da0cc13b89df68e4b27fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-29ace4cf19de37bcc077Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001325
FooDB IDFDB022556
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID42542
BioCyc IDN6N6N6-TRIMETHYL-L-LYSINE
METLIN ID6161
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389120
ChEBI ID17311
PubChem Compound ID440120
Kegg Compound IDC03793
YMDB IDNot Available
ECMDB IDM2MDB004580
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Chen F M; Benoiton N L A synthesis of N6,N6,N6-trimethyl-L-lysine dioxalate in gram amounts. Biochemistry and cell biology = Biochimie et biologie cellulaire (1986), 64(3), 182-3.
2. Inoue R, Miyake M, Kanazawa A, Sato M, Kakimoto Y: Decrease of 3-methylhistidine and increase of NG,NG-dimethylarginine in the urine of patients with muscular dystrophy. Metabolism. 1979 Aug;28(8):801-4.
3. Mizobuchi M, Miyake M, Sano A, Kakimoto Y: High concentration of free trimethyllysine in red blood cells. Biochim Biophys Acta. 1990 Feb 26;1033(2):119-23.
4. Minkler PE, Erdos EA, Ingalls ST, Griffin RL, Hoppel CL: Improved high-performance liquid chromatographic method for the determination of 6-N,N,N-trimethyllysine in plasma and urine: biomedical application of chromatographic figures of merit and amine mobile phase modifiers. J Chromatogr. 1986 Aug 2;380(2):285-99.
5. Lehman LJ, Olson AL, Rebouche CJ: Measurement of epsilon-N-trimethyllysine in human blood plasma and urine. Anal Biochem. 1987 Apr;162(1):137-42.
6. Park KS, Lee HW, Hong SY, Shin S, Kim S, Paik WK: Determination of methylated amino acids in human serum by high-performance liquid chromatography. J Chromatogr. 1988 May 25;440:225-30.
7. Terada N, Inoue F, Okochi M, Nakajima H, Kizaki Z, Kinugasa A, Sawada T: Measurement of carnitine precursors, epsilon-trimethyllysine and gamma-butyrobetaine in human serum by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):89-95.
8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.